(S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate → (S)-tert-butyl 1-amino-3-cyclohexylpropan-2-ylcarbamate

HRID 451730Notes

Reaction equation

HRID 451730 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 59382971(S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate

Product 1

HCID 10988904(S)-tert-butyl 1-amino-3-cyclohexylpropan-2-ylcarbamateYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate (13.6 g, 0.048 mol) and Pd/C (1.4 g) in methanol (200 mL) was hydrogenated with a balloon overnight. The mixture was filtered through a pad of Celite and the solvent was removed to give (S)-tert-butyl 1-amino-3-cyclohexylpropan-2-ylcarbamate (10.5 g, 86%), which was used in the next step without purification. 1H NMR (400 MHz, CDCl3): 4.52 (d, J=8.4 Hz, 1H), 3.68 (m, 2H), 2.73 (dd, J=13.6&4.4 Hz, 1H), 2.58 (dd, J=13.6&6.0 Hz, 1H), 1.81 (m, 1H), 1.65 (m, 4H), 1.42 (s, 9H), 1.40-1.00 (m, 6H), 1.00-0.70 (m, 2H). MS (E/Z): 257 (M+H+).

Workup

  1. customwas hydrogenated with a balloon overnight
  2. filtrationThe mixture was filtered through a pad of Celite
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-a2b77c454cc240fe89f05902b803a89a
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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